9-[3-[6-[[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-hydroxy-3-methylbutoxy]furo[3,2-g]chromen-7-one

Details

• Internal ID: 324cf224-da98-49a1-a642-0f281317fdef
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: 9-[3-[6-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-2-hydroxy-3-methylbutoxy]furo[3,2-g]chromen-7-one
• SMILES (Canonical): CC(C)(C(COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)O)OC4C(C(C(C(O4)COC5C(C(CO5)(CO)O)O)O)O)O
• SMILES (Isomeric): CC(C)(C(COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)O)OC4C(C(C(C(O4)COC5C(C(CO5)(CO)O)O)O)O)O
• InChI: InChI=1S/C27H34O15/c1-26(2,15(29)9-37-22-20-13(5-6-36-20)7-12-3-4-16(30)41-21(12)22)42-24-19(33)18(32)17(31)14(40-24)8-38-25-23(34)27(35,10-28)11-39-25/h3-7,14-15,17-19,23-25,28-29,31-35H,8-11H2,1-2H3
• InChI Key: AGQARHVGJIEPHM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₅
• Molecular Weight: 598.50 g/mol
• Exact Mass: 598.18977037 g/mol
• Topological Polar Surface Area (TPSA): 227.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.66
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 10

Synonyms

• Heraclenol 3'-O-[beta-D-apiofuranosyl-(1-6)-beta-D-glucopyranoside]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7476	74.76%
Caco-2	-	0.8703	87.03%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7042	70.42%
OATP2B1 inhibitior	-	0.8596	85.96%
OATP1B1 inhibitior	+	0.8948	89.48%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6737	67.37%
P-glycoprotein inhibitior	+	0.5877	58.77%
P-glycoprotein substrate	+	0.5060	50.60%
CYP3A4 substrate	+	0.6641	66.41%
CYP2C9 substrate	-	0.8330	83.30%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.9337	93.37%
CYP2C9 inhibition	-	0.9325	93.25%
CYP2C19 inhibition	-	0.8920	89.20%
CYP2D6 inhibition	-	0.9059	90.59%
CYP1A2 inhibition	-	0.8589	85.89%
CYP2C8 inhibition	+	0.5875	58.75%
CYP inhibitory promiscuity	-	0.8885	88.85%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6187	61.87%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9282	92.82%
Skin irritation	-	0.8007	80.07%
Skin corrosion	-	0.9502	95.02%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4126	41.26%
Micronuclear	-	0.6126	61.26%
Hepatotoxicity	+	0.6552	65.52%
skin sensitisation	-	0.8656	86.56%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8122	81.22%
Acute Oral Toxicity (c)	III	0.5176	51.76%
Estrogen receptor binding	+	0.8070	80.70%
Androgen receptor binding	+	0.7051	70.51%
Thyroid receptor binding	+	0.5523	55.23%
Glucocorticoid receptor binding	+	0.6179	61.79%
Aromatase binding	+	0.6907	69.07%
PPAR gamma	+	0.7409	74.09%
Honey bee toxicity	-	0.7608	76.08%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9310	93.10%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.08%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.96%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.27%	94.00%
CHEMBL4040	P28482	MAP kinase ERK2	94.92%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.35%	97.25%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	92.95%	95.83%
CHEMBL1937	Q92769	Histone deacetylase 2	92.37%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.14%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.26%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.20%	97.09%
CHEMBL4581	P52732	Kinesin-like protein 1	89.83%	93.18%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.76%	99.23%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	89.62%	95.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.07%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.48%	94.73%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	86.39%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.36%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.33%	86.33%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.85%	97.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.47%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.64%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.03%	96.09%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	82.85%	96.69%
CHEMBL226	P30542	Adenosine A1 receptor	82.81%	95.93%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.42%	96.90%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.24%	93.04%
CHEMBL4208	P20618	Proteasome component C5	81.98%	90.00%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.53%	80.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.36%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.12%	99.15%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.86%	96.67%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.77%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.37%	95.89%

Plants that contains it

• Heracleum candicans

Cross-Links

• PubChem: 73088243
• LOTUS: LTS0189588
• wikiData: Q104911974